Life, death, and free culture in the Mission

Ilya Zhitomirskiy was supposed to be the next Mark Zuckerberg. He had the startup, the crowdfunding, the loyal following. And then everything fell apart.

By Matthew Shaer

FORTUNE — At 8 p.m. on Nov. 12, 2011, a San Francisco entrepreneur named Tony Lai received a call from a number he did not recognize. Lai had recently returned from a trip to Costco to pick up party supplies — he and a friend had planned a joint birthday bash that night — and he set down his bags in the hallway and pressed the answer button on his phone. The voice on the other end was panicked, afraid. After a while, Lai hung up and walked to the next room, where one of his roommates, Gardner Bickford, was lying in bed, reading.

“That was Ilya’s mom,” Lai said. “She can’t reach Ilya.”

Lai, a soft-spoken former lawyer, was then living on the third floor of a shambling house on Treat Avenue in the Mission. The Hive, as the place is known, has long played host to a rotating cast of free-spirited programmers and innovators, many of whom come to San Francisco to escape what they regard as the stultifying atmosphere of Silicon Valley proper. The residents of the Hive tend to be young and male, and disdainful of the traditional startup route: build, sell, repeat.

“In this community it’s not about the windfalls,” says one Mission resident. “If you can create something of value that helps other people — if you can make an impact — that’s what garners respect.”

Lai shared his apartment with three friends: Bickford, a coder at Adobe (ADBE ); David Kettler, a recent graduate of Stanford; and Ilya Zhitomirskiy, the co-founder of Diaspora, an open-source social network that many believed could eventually topple Facebook (FB ). Although they had been roommates for only a few short months, the four men had become extremely close, bonding over their interest in digital rights and free culture, a movement which seeks to “liberate” information from the grips of big media companies.

At 21, Zhitomirskiy was the youngest of the group and in many ways the most idealistic. Perhaps he was now parked in front of his laptop, his roommates reasoned, hammering on the beta build of Diaspora.

“Let’s just knock,” Bickford said.

MORE: 50 greatest business rivalries of all time
Iilya Zhitomirskiy.

Iilya Zhitomirskiy.

But there was no answer, and the doorknob wouldn’t budge. Bickford used his fingernail to pop the pushbutton lock. Zhitomirskiy lay on his back on the bed, a black bag pulled over his head. A line of tubing connected the bag to a cylindrical helium canister on the floor.

Nearby was a Post-it note, which read, “Thanks everyone for everything. This was my decision alone.”

The meaning of any suicide is the secret stolen with the life lost. And yet in the months following his death, Zhitomirskiy’s inner circle struggled to make sense of the tragedy. Zhitomirskiy had been a genuine rock star in tech circles — the “free culture equivalent of Mark Zuckerberg,” to quote one friend. He had a cadre of admirers and a startup the world was watching. And yet he struggled with depression and anxiety and with the sense that his goals were in some way incompatible with the cash-first ethos of Silicon Valley. His company, Diaspora, eventually foundered — its very premise turned into its greatest weakness, for how do you monetize a social network that refuses to mine for profit the personal data of its users?

Zhitomirskiy worked very hard but always felt he wasn’t working hard enough. And in a place filled with dreamers, where success is measured in venture capital funding and user bases, he eventually lost his way.

What follows is an account of the last year and a half of his life. It is based primarily on medical and police records and the memories of Zhitomirskiy’s friends, acquaintances, and former roommates, who agreed to be interviewed — in most cases on the record.

The dragons
Ilya Zhitomirskiy had always been a dreamer. He was born in Moscow in 1989 to a successful mathematician father, whose own father was a mathematician. In 2000 he moved with his family to the U.S., first to Massachusetts, and then to Louisiana, and finally to Ardmore, a leafy suburb of Philadelphia. At Lower Merion High School he joined the robotics team and excelled in math and science. He was outgoing and popular with both teachers and peers. “He always made you feel better, always positive, friendly and sweet,” a classmate recalled.

After graduation Zhitomirskiy spent a semester at Tulane, in New Orleans, before transferring to New York University, where he majored in mathematics. It was there, thanks to a few influential teachers, that he became enraptured by Free Culture. The way Free Culture activists see it, culture — defined as books, music, movies, and web properties — “wants” to be free. It is only the corporate entities that insist on commodifying it.

Zhitomirskiy traveled frequently to Free Culture conferences in New York and Berkeley, and befriended activists at the Electronic Frontier Foundation, a kind of ACLU for digital rights. (In this way he shared much in common with Aaron Swartz , another brilliant idealist whose life was recently cut short by suicide.) He developed a colorful theory of the “dragons” threatening modern society. The dragons stood for the corporations, he explained to his friends. If a corporation controlled culture, then culture was no longer free. The recording industry, the Internet service providers, the media monopolies, the tech conglomerates: dragons all.

His friend Parker Phinney, who met Zhitomirskiy at a conference at MIT, recalled him saying, “Okay, I’m going to spend my time slaying Google. Now let’s find you a dragon to slay.”

Zhitomirskiy was a natural communicator. Short and lithe, with a shock of light brown hair, he had an easy smile and hands that he had trouble keeping at his side. He dressed loudly, in bright colors and tie-dyed T-shirts. Girls loved him. “I was more instantly attracted to Ilya than I ever have been to anyone,” says Stephanie Lewkiewicz, a girlfriend at NYU. “He just had this energy about him. I’m still at a loss to explain it.”

In February of 2010, Zhitomirskiy attended a lecture given by Eben Moglen, a professor of law at Columbia and a hero of the Free Culture movement. Moglen, like Zhitomirskiy, believed that there was great power in the tech community, if it could be channeled into something meaningful.

At this lecture, Moglen encouraged the members of the audience to create social media products that did not violate user privacy. Together with three friends from NYU — Maxwell Salzberg, Daniel Grippi, and Raphael Sofaer — Zhitomirskiy decided to take Moglen up on his challenge.

The plan was simple: build a decentralized social network controlled by the users themselves. Facebook kept its users’ personal information on servers owned by Facebook and sold the information to advertisers. Diaspora would allow all its users to own all their data. While Facebook was closed, controlled in a top-down manner, Diaspora would be wide open, controlled from the bottom up. As a logo, Salzberg, Grippi, Sofaer, and Zhitomirskiy chose an asterisk, or a “seed” — the idea being that the billions of social network users in the world could take their kernels of private info and store it away on their own terms, either in the cloud or on their hard drives.

The decentralized social network is not new. In 2004, for instance, the developer Michael Chisari had introduced Appleseed, an open-source conglomeration of individually operated “nodes” — not so different from Diaspora’s “seeds.” But Chisari struggled to draw attention to Appleseed. Salzberg, Grippi, Sofaer, and Zhitomirskiy never had that problem.

MORE: Yes we cannabis
Zhitomirskiy at the Hive.

Zhitomirskiy at the Hive.

They were young and appealingly tousled, and they knew how to leverage existing social media channels. They talked up their project on Twitter and Facebook, and in April 2010, they posted a video to the crowdfunding site Kickstarter, asking for donations.

Their timing was perfect. Earlier that year Facebook had come under fire for surreptitiously changing its privacy settings. People wanted out. The Times put a story on Diaspora atop its homepage, and $200,000 poured in, then a Kickstarter record. Venture capital firms wanted face time.

In May the Diaspora founders flew to San Francisco. Grippi and Salzberg had just graduated; Sofaer, a sophomore, and Zhitomirskiy, a junior, planned on taking some time off from school while they all worked on Diaspora full-time. He had found a new dragon to slay: Facebook.

The code
The Diaspora team arrived in the city in late spring, when the parks are full and a brisk ocean breeze blows through the middle of town. Sofaer found an apartment in the Mission, and the other three founders moved into separate rooms at a dilapidated boardinghouse near Union Square.

They had a clear-cut goal — the release of the source code — and money enough to last for months. From 10 in the morning to seven at night and sometimes later, the members of the Diaspora team sat hunched over their desks at the back of Pivotal Labs, the startup consultancy that employed Raphael’s brother, Mike.

At first things moved slowly. Coding is an inherently lonely science, and even when the project is a team effort and there is a larger goal in sight, as there was with Diaspora, at the end of the day each member of the team must conduct his own battle with the screen and keyboard, and the lines of #starts and #ends and validations that seem to cascade into infinity.

Salzberg and Grippi had majored in computer science at NYU. And Sofaer had dabbled in coding as a kid. But Zhitomirskiy had almost no programming experience at all — he was teaching himself from scratch.

MORE: Corporate America: We’re junk and we like it

He grew frustrated easily. Mathematics, his first love, was durable and concrete. Programming was fragile. It was easy enough to summon an idea and erect the scaffolding of HTML around it, but there were always bugs — microscopic defects, tiny niggling glitches in the infrastructure that, if you weren’t careful, could crash the whole operation.

By midsummer — an admittedly short time for such an ambitious project — the 6,000 donors who had contributed cash to Diaspora on Kickstarter were getting anxious. The company was accused of shilling “vaporware” — a much ballyhooed product that never actually sees a public release.

Raphael Sofaer said the team felt the pressure acutely. Still, he added, the constant scrutiny “brought us advantages too.” One of those advantages was the full-time counsel of experienced entrepreneurs such as Janice Fraser, the head of LUXr, a San Francisco company that agreed to help coach Diaspora in the summer of 2010.

“If you’re a first-time entrepreneur and suddenly you’re being courted by the [big venture capital firms], it can be head-churning,” Fraser says. Fraser helped the group develop both its product and a pitch for potential investors.

Still, Fraser, whose mother and siblings have struggled with schizophrenia, said she kept her emotional distance from Zhitomirskiy. “With Ilya, I instantly recognized a type … a magnetic personality that comes at a price,” she said. “I’m not a psychiatrist, but I know from firsthand experience that absolute delightfulness goes hand in hand with darkness.”

The sickness
To many of his friends, Zhitomirskiy seemed relentlessly happy, unflaggingly upbeat, full of “optimism for a future that only he could see,” as one put it. Stephanie Lewkiewicz told me she had been daunted by the collegiate grind while “Ilya just sort of cruised through.”

But Zhitomirskiy had long battled depression and anxiety, and in San Francisco his symptoms became more noticeable. Raphael Sofaer recalls that at one point in August, the four founders of Diaspora went to go catch a screening of Scott Pilgrim vs. the World – a good way to blow off some steam. But Zhitomirskiy fidgeted through the previews, and when the film started, he stood up and marched out of the theater.

MORE: Where is China headed now?

Later Zhitomirskiy told Michael Sofaer that he was worried he was weighing down the rest of the team. He was an inferior coder, he said. “I told him that he was the moral compass of the organization — in some ways the true spirit of the group,” Sofaer recalls. “He was contributing so much, far too much to worry that lines of code should be a measure of his contribution to the world.”

In September the Diaspora team released the source code — a major milestone for the project. No longer could Diaspora be slagged off as vaporware. And yet by inviting other programmers to contribute to the project, the team was also inviting them to vet it for flaws. Diaspora, a prominent security professional told me recently, “was considered Swiss cheese. It had all the textbook security and privacy vulnerabilities of something that was created by college kids.”

On Twitter the developer Patrick McKenzie warned users not to host the project, which he pronounced “screamingly unsafe.” “Code for open-source Facebook littered with land mines,” read the headline in the Register, a popular tech site. The Diaspora founders went back to the drawing board.

In October, Zhitomirskiy answered a Craigslist ad for a room in the Hive. When Bickford showed Zhitomirskiy through one of the downstairs apartments, “some people were baking bread and others were drinking beer in the backyard, and Ilya was like, ‘This is so awesome. I want to live here,’ ” Bickford remembered.

Zhitomirskiy put down the first month’s rent immediately. But a few weeks later he flew home to Pennsylvania. While he was there he was diagnosed with depression and bipolar disorder; he also confided to his family that he was considering suicide. In a report assembled by investigators after his death, Zhitomirskiy’s father, Alexei, is quoted as saying that Ilya traveled briefly to Boston, where he saw a psychiatrist. He was prescribed a wide range of pills that eventually came to include lithium, which is used to treat mania, and Klonopin, a powerful benzodiazepine.

He spent much of his time at home with his mother and father and little sister. He spoke frequently to Lewkiewicz, his ex-girlfriend. Although it had been Zhitomirskiy who ended the relationship, he would later tell friends that Lewkiewicz was the love of his life. He seemed to find solace in their conversations. By that time Lewkiewicz had moved on to UCLA, where she had been accepted into the Ph.D. program in mathematics.

MORE: Apple’s new $13.5 billion revenue stream

Zhitomirskiy was envious. He talked openly about re-applying to NYU.

“When he first became depressed,” Lewkiewicz says, “his plan was definitely to return to school — to quit Diaspora.” If he had stayed on the East Coast, she added, “I think one hundred percent it all would have turned out very differently.”

Second chances
In November, with Zhitomirskiy in Pennsylvania, the other three founders had released a “private alpha” to a scattering of peers. Three months later, in January 2011, Zhitomirskiy flew back to San Francisco, and the entire team began to chart a course to the beta launch, where a larger number of users would be invited to try out the network.

They were walking a thin line. Diaspora had to be accessible enough to be operable by the average computer user and at the same time uphold its original mission statement. The irony did not escape Zhitomirskiy. The qualities that made Facebook repellent to Free Culture partisans — the stockpiling of personal information, the lack of privacy — were the very things that attracted casual users to the social network. “It was a huge Catch-22,” says someone intimately involved in the business operations of the company. “And they knew it.”

In the late spring Zhitomirskiy ditched his original room in the Hive for a larger one at the end of the hall. The windows overlooked the courtyard. In the evenings, when the fog lifted, he could see the soft white lights of the houses on Potero Hill. In his spare time he rode his pockmarked gray Schwinn 10-speed to Noisebridge, a hacker collective in the heart of the Mission. He told the other members to “hack their defaults” — to override their inherited habits and build something better out of themselves. He recited his favorite mantras aloud: “Gather epic people and make unreasonable demands” and “Begin with love, proceed analytically from there.”

The trip to the East Coast had clearly invigorated Zhitomirskiy, friends recalled. He was happier, more alive. The pills were working. When anyone asked where he’d been the last couple of months, he would murmur something about a medical leave. Zhitomirskiy told Lewkiewicz that NYU would be waiting if he wanted to return. “That was part of the rationale,” she told me. “That he could always go back.”

By July, Diaspora had depleted the $200,000 in Kickstarter funds, and the team began ­casting around for alternate funding sources. A year earlier, while the team was still in New York, several venture capital firms had approached Diaspora, including Kleiner Perkins Caufield & Byers. Diaspora had resisted these overtures, partially because it seemed antithetical to the grass-roots nature of the project, and mostly because there wasn’t really much product to show. Now, however, Diaspora had a working alpha build.

MORE: 10 women business leaders, 64 smart travel tips

Still, early meetings went nowhere. According to one insider with knowledge of the talks, the VCs were particularly exasperated by the lack of a Diaspora business model — it was one thing, after all, to cook up a counterculture Facebook, and another to actually make it lucrative. Diaspora, which had been conceived not as a product but as a revolution, was bumping up against the stark realities of Silicon Valley: Without a potential revenue stream, even the most promising projects will eventually fall apart.

This realization seems to have stunned Zhitomirskiy. “None of [the founders] had a way to turn something so focused on killing business models into a business,” Kettler says.

In July, Grippi, Sofaer, and Zhitomirskiy invited Yosem Companys to a sit-down at Sofaer’s father’s house in Palo Alto. Companys, a large and cheery Ph.D. candidate at Stanford, had been in touch with the Diaspora founders for more than a year. Like Zhitomirskiy, Companys was deeply involved in free culture causes and saw Diaspora as a way of liberating the social web. He agreed to join Diaspora as an adviser.

Over the next few months Companys and the Diaspora team explored a range of potential strategies. One involved charging privacy-minded users a low monthly fee to rent their own servers. In this scenario Diaspora, which didn’t actually own any servers, would act as the middleman, pocketing a few bucks with every subscription. Another possibility was to partner with a like-minded organization such as Mozilla, the makers of the open-source browser Firefox. Eventually Companys was able to stir up interest among a group of angel investors in Singapore, who would invest $1 million in Diaspora. Nothing came of it.

Arguments among the team members became more common; Salzberg, in particular, clashed repeatedly with Companys over a series of botched fundraising efforts. Diaspora was entering the most crucial phase in its history, and yet the company seemed in danger of fissuring from within.

And then a fresh calamity: At the I/O developers conference in San Francisco, Google (GOOG ) introduced the social network Google Plus. One of the key features of Google Plus was something called Circles, which allowed users to arrange their contacts into groups — friends or family or co-workers — and control the amount of information each group could see.

As Zhitomirskiy was quick to point out, Circles had a lot in common with Aspects, a key plank of the Diaspora platform. In fact, the two were almost identical. Zhitomirskiy wondered aloud if Google had stolen from him; the entire team, according to one friend, was “devastated.”

In August, Diaspora took to Twitter to announce that a beta launch was on the way. The alpha build had been a qualified success for Diaspora — tens of thousands of users signed on to Diaspora every week, many of them in Europe. But for every word of encouragement, there was a torrent of criticism. Plenty of users had developed a deep ideological connection to the platform, and when they felt their suggestions or comments were being ignored, they would reach out to the founders themselves — Ilya, one friend said, was often deluged with “aggressive” forum postings and e-mails.

At the end of August, roughly two months before his death, Zhitomirskiy traveled with several friends to the Burning Man festival, where he delivered a well-received speech on digital rights. Then he changed into a flying-squirrel onesie and waltzed around the outskirts of camp until the hard desert sun washed over the crest of the Nevada plains.

The fall
October, by contrast, was cold and damp. Zhitomirskiy spent much of his time inside, in front of the computer screen. Diaspora was late with the beta launch, and weeks earlier Raphael Sofaer had decided to fly back east and re-enroll at NYU, leaving just Zhitomirskiy, Grippi, and Companys. Mike Sofaer told me that his brother had always planned on treating Diaspora like a temporary project, but others say that Zhitomirskiy found Raphael’s departure demoralizing.

Zhitomirskiy talked more frequently about going back to school, perhaps at Stanford, where Kettler and Lai had both studied. But that would have been tantamount to surrender. He would see the project through.

On Oct. 12, Diaspora sent an e-mail to its users, asking for donations of $25 or more. By then an infusion of major VC cash was a pipe dream. Diaspora just needed a few thousand bucks — enough for them to work out the remaining problems in the interface.

Despite a few jabs from the tech press — “Diaspora asking for money, again,” groaned a writer for BetaBeat — Diaspora did succeed in attracting $45,000 in donations. The money was slow to come through: PayPal temporarily froze Diaspora’s account, preventing the team from accessing the funds. (PayPal later apologized, calling it a glitch.)

In early October the Hive held a birthday party for Zhitomirskiy. He was turning 22. He looked terrible. “It was clear he wasn’t taking care of himself,” one friend said. Part of the issue may have been medical — there is evidence to suggest that by October, Zhitomirskiy had drastically altered his drug regimen. During one call, he told Lewkiewicz that the drugs were “numbing him, sedating him without improving his mood. He was disappointed with that,” Lewkiewicz said. “He felt like his mind was clouded.”

When the San Francisco medical examiner conducted its autopsy, it found in Zhitomirskiy’s blood only trace amounts of citalopram, the active ingredient in the anti-depressant Celexa — a far cry from the drug cocktail that Zhitomirskiy had originally been prescribed.

Everywhere he turned, Zhitomirskiy believed he could see evidence of his own ineptitude. On Nov. 7 the website of the Wall Street Journal published a short article on Diaspora. The headline: WHAT EVER HAPPENED TO DIASPORA, THE “FACEBOOK KILLER”? His in-box spilled over with inquiries from fans. What was taking so long, anyway? At some point on Nov. 9, Zhitomirskiy phoned his mother. She must have heard something in his voice. Two days later, when she called Tony Lai looking for her son, she was distraught.

On Thursday, Nov. 10, Zhitomirskiy walked to a party shop in the Mission and purchased a canister of helium. The next night, a Friday, he locked himself into his room, lay down on his bed, and pulled a black bag over his head. He connected a line of plastic tubing to the canister and threw the switch. He was dead within minutes.

On Dec. 16, Zhitomirskiy was buried in West Laurel Hill Cemetery, in Lower Merion, Pa. Five months later, on April 16, 2012, the San Francisco medical examiner officially ruled Zhitomirskiy’s death a suicide. The coroner’s report stated that Zhitomirskiy had killed himself using an “exit bag.” Unlike other forms of suicide, the exit bag is entirely painless — the helium acts as a tranquilizer, preventing the victim from tearing off the plastic when he or she begins to suffocate.

An encouraging ghost
On a cool evening in August, I visited Gardner Bickford, Zhitomirskiy’s former roommate, at the Hive. The courtyard was scattered with rain-mottled couches and broken heat lamps.

Bickford rummaged under one of the staircases, and held forward a gray Schwinn 10-speed with tattered grips. He and Michael Sofaer had plans to turn Ilya’s old bike into a twisted metal sculpture that they would bring with them to Burning Man. “I think Ilya would appreciate that,” Bickford smiled.

I followed him to the third-floor apartment, where his girlfriend, Rachel, was cooking dinner. In the weeks after Zhitomirskiy’s suicide, the third floor of the Hive had been empty. None of the remaining roommates could bear to be around. Bickford and Kettler holed up with their girlfriends, and Lai took to staying with friends in Palo Alto.

Then, last January, Bickford managed to temporarily rent Zhitomirskiy’s old room to a tall Dutch programmer named Kasper Souren. Souren had only one request: that Bickford tell him exactly how Zhitomirskiy had died. Bickford complied, and Souren moved in for a four-week stretch, breaking the pall that hung over the house.

Once Souren was gone, Bickford and Rachel took the room for themselves. It felt like time, Bickford told me. They’d brought in their own furniture, but the setup was the same — a desk tucked into the bay windows, the bed facing the door. We walked back into the hall, and Bickford pointed at a framed piece of lined writing paper.

“The List of Things That Need to Be Done,” the top of the paper read. Lai, Bickford, and Kettler had all contributed to the list, but many of the ideas were Ilya’s: “Repeal one unhealthy local law”; “regular Hive meetings”; “Hive murals”; “remove bribery from Congress.”

Rachel opened the oven, and the smell of warm pie filled the kitchen. She was cooking rhubarb for the first time. We ate standing around the island. I asked Gardner if it ever felt strange living in the room that his friend had once occupied. He paused. “In the beginning,” he said, “I wondered if there was a ghost in there. But then I figured if it was a ghost, it would be at least be an encouraging one, you know?”

Last August, Daniel Grippi and Maxwell Salzberg announced that they would halt work on Diaspora. They promised that the site would live on in the hands of its supporters — “the goal,” they wrote on the Diaspora blog, “is to make this an entirely community-driven and community-run project.”

Surprisingly, a significant number of users, many of them centered in Europe, have taken Grippi and Salzberg up on their offer, and although the founders no longer have an active role in development, the site has continued to grow.